(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-tert-butyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]but-3-en-2-one

Base Information

Chemical Name:(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-tert-butyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]but-3-en-2-one
CAS No.:476156-44-2
Molecular Formula:C₄₄H₅₃NO₆Si
Molecular Weight:719.993
Hs Code.:

Synonyms:(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-tert-butyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]but-3-en-2-one

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Chemical Property of (E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-tert-butyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]but-3-en-2-one

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Technology Process of (E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-tert-butyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]but-3-en-2-one

There total 2 articles about (E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-tert-butyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]but-3-en-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 476156-42-0
(2R,3R,4R,5R)-3,4-dibenzyloxy-N-tert-butyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

: 476156-44-2
(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-tert-butyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 4 Angstroem molecular sieves; NMO; TPAP / CH₂Cl₂ / 2 h / 20 °C

2: 380 mg / toluene / 24 h / Heating

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; toluene; 2: Wittig reaction;
DOI:10.1016/S0957-4166(02)00408-1

Reference yield:

: 1439-36-7
1-triphenylphosphoranylidene-2-propanone

: 476156-43-1
[(2'S,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-tert-butyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]carbaldehyde

: 476156-44-2
(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-tert-butyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: In toluene; for 24h; Heating;
DOI:10.1016/S0957-4166(02)00408-1

Reference yield:

: 476156-44-2
(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-tert-butyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]but-3-en-2-one

: 476156-45-3
tert-butyl [(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-(3-oxobutyl)]pyrrolidine-1-carboxylate

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 12h; under 3040 Torr;
DOI:10.1016/S0957-4166(02)00408-1